[go: up one dir, main page]

EP0382716B1 - Use of commercial lecithin as skin penetration enhancer - Google Patents

Use of commercial lecithin as skin penetration enhancer Download PDF

Info

Publication number
EP0382716B1
EP0382716B1 EP88903109A EP88903109A EP0382716B1 EP 0382716 B1 EP0382716 B1 EP 0382716B1 EP 88903109 A EP88903109 A EP 88903109A EP 88903109 A EP88903109 A EP 88903109A EP 0382716 B1 EP0382716 B1 EP 0382716B1
Authority
EP
European Patent Office
Prior art keywords
active ingredient
lecithin
use according
effective amount
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP88903109A
Other languages
German (de)
French (fr)
Other versions
EP0382716B2 (en
EP0382716A1 (en
Inventor
Mahdi Fawzi
Uma R. Iyer
Majid Mahjour
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Co LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21895652&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0382716(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC
Priority to AT88903109T priority Critical patent/ATE99960T1/en
Publication of EP0382716A1 publication Critical patent/EP0382716A1/en
Publication of EP0382716B1 publication Critical patent/EP0382716B1/en
Application granted granted Critical
Publication of EP0382716B2 publication Critical patent/EP0382716B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • Lecithin as used in commerce, is the name given to a group of substances present in fats which are obtained mainly from oil seeds, for example, soybeans and rape seeds) and from egg yolks.
  • Commercial lecithin is a natural emulsifying agent used in foodstuffs and pharmaceutical products, for example, in creams, balms, or ointments.
  • Lecithin has also been described in dispersions or suspensions in propellants.
  • bronchodilators can be administered by inhalation means in a propellant containing lecithin.
  • an object of the present invention is a method of administering a drug transdermally or transmucosally by using lecithin in the pharmaceutical composition.
  • the present invention relates to a pharmaceutical composition adapted for transdermal or transmucosal administration comprising an active ingredient and an effective amount of lecithin.
  • Transdermal pharmaceutical compositions are used as a means for avoiding the uncertainties of oral administration and the inconvenience of administration by rejection.
  • An active ingredient for purposes of the present invention is an effective amount of any therapeutically active drug.
  • Preferred drugs are those which find application in various therapeutic uses such as antihypertensives, analgesics, antitussives, antihistamines, bronchodilators and cognition activators. Therefore, the lecithin compositions are expected to be useful in drugs such as procaterol, dextromethorphan, oxymorphone and diphenhydramine.
  • the lecithin employed by the present invention is commercial lecithin or soy lecithin, for example, Lucas Meyer, Inc. commercial soy lecithins such as Epikuron TI 135F and Capcithin TM 50-R.
  • the amount of lecithin used in the transdermal formulations may vary depending on the amount of active ingredient needed and the use of other excipients.
  • a useful range of lecithin found to be effective for penetration enhancement is about 2 to about 40% by weight of the composition. Preferred is from about 5 to about 10%.
  • the present composition also may contain pharmaceutically acceptable excipients. These are, for example, tetraglycol (TG), alcohols, glycols, fatty acids, triacetin and silicon fluids.
  • TG tetraglycol
  • alcohols for example, alcohols, glycols, fatty acids, triacetin and silicon fluids.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Dermatology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

A method of enhancing penetration of a drug through the skin or other biological membranes using lecithin is herein described along with pharmaceutical compositions containing effective amounts of lecithin as a penetration enhancer.

Description

  • Lecithin, as used in commerce, is the name given to a group of substances present in fats which are obtained mainly from oil seeds, for example, soybeans and rape seeds) and from egg yolks. Commercial lecithin is a natural emulsifying agent used in foodstuffs and pharmaceutical products, for example, in creams, balms, or ointments.
  • Lecithin has also been described in dispersions or suspensions in propellants. For example, bronchodilators can be administered by inhalation means in a propellant containing lecithin.
  • It has now been found that lecithin enhances the penetration of a drug through the skin and across other biological membranes, such as intestinal, buccal, rectal, and nasal. Thus an object of the present invention is a method of administering a drug transdermally or transmucosally by using lecithin in the pharmaceutical composition.
  • Accordingly, the present invention relates to a pharmaceutical composition adapted for transdermal or transmucosal administration comprising an active ingredient and an effective amount of lecithin.
  • Transdermal pharmaceutical compositions are used as a means for avoiding the uncertainties of oral administration and the inconvenience of administration by rejection.
  • An active ingredient for purposes of the present invention is an effective amount of any therapeutically active drug.
  • Preferred drugs are those which find application in various therapeutic uses such as antihypertensives, analgesics, antitussives, antihistamines, bronchodilators and cognition activators. Therefore, the lecithin compositions are expected to be useful in drugs such as procaterol, dextromethorphan, oxymorphone and diphenhydramine.
  • The lecithin employed by the present invention is commercial lecithin or soy lecithin, for example, Lucas Meyer, Inc. commercial soy lecithins such as Epikuron TI 135F and Capcithin TM 50-R. The amount of lecithin used in the transdermal formulations may vary depending on the amount of active ingredient needed and the use of other excipients. A useful range of lecithin found to be effective for penetration enhancement is about 2 to about 40% by weight of the composition. Preferred is from about 5 to about 10%.
  • The present composition also may contain pharmaceutically acceptable excipients. These are, for example, tetraglycol (TG), alcohols, glycols, fatty acids, triacetin and silicon fluids.
  • The following examples in table form are illustrative of the present invention where the use of commercial soy lecithin was found to enhance penetration of various drugs through mouse skin.
    Figure imgb0001

Claims (20)

1. A pharmaceutical composition adapted for transdermal or transmucosal administration comprising a therapeutically effective amount of an active ingredient, an effective amount of commercial soy bean lecithin, and one or more pharmaceutically acceptable excipients.
2. A composition according to claim 1, wherein the amount of lecithin is 2 to 40 %.
3. A composition according to claim 1, wherein the amount of lecithin is 5 to 10 %.
4. A composition according to claim 1, wherein the active ingredient is diphenhydramine.
5. A composition according to claim 1, wherein the active ingredient is dextromethorphan.
6. A composition according to claim 1, wherein the active ingredient is oxymorphone.
7. A composition according to claim 1, wherein procaterol is the active ingredient.
8. Use of commercial soy bean lecithin for the manufacture of pharmaceutical compositions enhancing penetration of a drug through the skin or other biological membrane, wherein the pharmaceutical compositions contain a therapeutically effective amount of an active ingredient, an effective amount of commercial soy bean lecithin and one or more pharmaceutically acceptable excipients.
9. Use according to claim 8, wherein the active ingredient is an antihypertensive.
10. Use according to claim 8, wherein the active ingredient is an antihistamine.
11. Use according to claim 8, wherein the active ingredient is an analgesic.
12. Use according to claim 8, wherein the active ingredient is an antitussive.
13. Use according to claim 8, wherein the active ingredient is a cognition activator.
14. Use according to claim 8, wherein the active ingredient is a bronchodilator.
15. Use according to claim 8, wherein the active ingredient is procaterol.
16. Use according to claim 8, wherein the active ingredient is diphenhydramine.
17. Use according to claim 8, wherein the active ingredient is dextromethorphan.
18. Use according to claim 8, wherein the active ingredient is oxymorphone.
19. Use according to claim 8, wherein the effective amount of lecithin is 2 to 40 %.
20. Use according to claims 8, wherein the effective amount of lecithin is 5 to 10 %.
EP88903109A 1987-04-13 1988-03-18 Use of commercial lecithin as skin penetration enhancer Expired - Lifetime EP0382716B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88903109T ATE99960T1 (en) 1987-04-13 1988-03-18 USE OF COMMERCIAL LECITHIN AS A SKIN PENETRATION ENHANCER.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US07/037,671 US4783450A (en) 1987-04-13 1987-04-13 Use of commercial lecithin as skin penetration enhancer
US37671 1987-04-13
PCT/US1988/000886 WO1988007871A1 (en) 1987-04-13 1988-03-18 Use of commercial lecithin as skin penetration enhancer

Publications (3)

Publication Number Publication Date
EP0382716A1 EP0382716A1 (en) 1990-08-22
EP0382716B1 true EP0382716B1 (en) 1994-01-12
EP0382716B2 EP0382716B2 (en) 1998-01-28

Family

ID=21895652

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88903109A Expired - Lifetime EP0382716B2 (en) 1987-04-13 1988-03-18 Use of commercial lecithin as skin penetration enhancer

Country Status (5)

Country Link
US (1) US4783450A (en)
EP (1) EP0382716B2 (en)
JP (1) JP2714413B2 (en)
DE (1) DE3887156T3 (en)
WO (1) WO1988007871A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7459171B2 (en) 1999-07-05 2008-12-02 Idea Ag Method for the improvement of transport across adaptable semi-permeable barriers
US7867480B1 (en) 1999-01-27 2011-01-11 Gregor Cevc Non-invasive vaccination through the skin
US7927622B1 (en) 1999-01-27 2011-04-19 Gregor Cevc Methods of transnasal transport/immunization with highly adaptable carriers

Families Citing this family (89)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4981681A (en) * 1988-08-26 1991-01-01 Vittorio Tosti Lotion mixture and method of treating psoriasis
US5059426A (en) * 1989-03-22 1991-10-22 Cygnus Therapeutic Systems Skin permeation enhancer compositions, and methods and transdermal systems associated therewith
US4973468A (en) * 1989-03-22 1990-11-27 Cygnus Research Corporation Skin permeation enhancer compositions
US5053227A (en) * 1989-03-22 1991-10-01 Cygnus Therapeutic Systems Skin permeation enhancer compositions, and methods and transdermal systems associated therewith
US5498607A (en) * 1990-07-30 1996-03-12 University Of Miami Treatment for hypercholesterolemia
WO1993011767A1 (en) * 1991-12-18 1993-06-24 Warner-Lambert Company Transdermal delivery of (e)-1,2,5,6-tetrahydro-1-methyl-3-pyridine-carboxaldehyde-o-methyloxine hcl and related compounds in the treatment of cognitive disorders and for analgesia
US5229130A (en) * 1991-12-20 1993-07-20 Cygnus Therapeutics Systems Vegetable oil-based skin permeation enhancer compositions, and associated methods and systems
DK0625899T3 (en) * 1992-02-12 1996-06-17 Janssen Cilag S P A Liposomal itraconazole formulations
US5505960A (en) * 1992-02-12 1996-04-09 Janssen Farmaceutici S.P.A. Liposomal piroxicam formulations
EP0625898B1 (en) * 1992-02-12 1996-05-15 JANSSEN-CILAG S.p.A. Liposomal piroxicam formulations
TW224048B (en) * 1992-03-30 1994-05-21 Hoechst Roussel Pharma
US5900250A (en) * 1992-05-13 1999-05-04 Alza Corporation Monoglyceride/lactate ester permeation enhancer for oxybutnin
AU679793B2 (en) * 1993-09-29 1997-07-10 Alza Corporation Monoglyceride/lactate ester permeation enhancer
US20020048596A1 (en) * 1994-12-30 2002-04-25 Gregor Cevc Preparation for the transport of an active substance across barriers
US5945409A (en) 1995-03-10 1999-08-31 Wilson T. Crandall Topical moisturizing composition and method
US5639740A (en) * 1995-03-10 1997-06-17 Crandall; Wilson Trafton Topical moisturizing composition and method
WO1997002041A1 (en) 1995-07-03 1997-01-23 Crandall Wilson T Transdermal and oral treatment of androgenic alopecia
SE9601528D0 (en) * 1996-04-23 1996-04-23 Pharmacia Ab Transdermally administered dextromethorphan as an antitissue agent
US5837289A (en) * 1996-07-23 1998-11-17 Grasela; John C. Transdermal delivery of medications using a combination of penetration enhancers
US5709878A (en) * 1996-08-02 1998-01-20 Rosenbaum; Jerry Transdermal delivery of dehydroepiandrosterone
US20060002949A1 (en) 1996-11-14 2006-01-05 Army Govt. Of The Usa, As Rep. By Secretary Of The Office Of The Command Judge Advocate, Hq Usamrmc. Transcutaneous immunization without heterologous adjuvant
US5980898A (en) 1996-11-14 1999-11-09 The United States Of America As Represented By The U.S. Army Medical Research & Material Command Adjuvant for transcutaneous immunization
US6797276B1 (en) 1996-11-14 2004-09-28 The United States Of America As Represented By The Secretary Of The Army Use of penetration enhancers and barrier disruption agents to enhance the transcutaneous immune response
US5885597A (en) * 1997-10-01 1999-03-23 Medical Research Industries,Inc. Topical composition for the relief of pain
GB2331924A (en) * 1997-12-08 1999-06-09 Phares Pharm Res Nv Lipid compositions and their use
US5869090A (en) * 1998-01-20 1999-02-09 Rosenbaum; Jerry Transdermal delivery of dehydroepiandrosterone
US6312703B1 (en) 1998-02-06 2001-11-06 Lecigel, Llc Compressed lecithin preparations
US5900249A (en) * 1998-02-09 1999-05-04 Smith; David J. Multicomponent pain relief topical medication
US6143278A (en) * 1998-02-23 2000-11-07 Elkhoury; George F. Topical application of opioid analgesic drugs such as morphine
US6011022A (en) * 1998-03-03 2000-01-04 El Khoury; George F. Topical application of muscarinic analgesic drugs such as neostigmine
MXPA01006424A (en) 1998-12-23 2002-06-04 Idea Ag Improved formulation for topical non-invasive application in vivo.
DE10024413A1 (en) * 2000-05-19 2001-12-06 Mika Pharma Gmbh Pharmaceutical and / or cosmetic preparation
US8980290B2 (en) * 2000-08-03 2015-03-17 Antares Pharma Ipl Ag Transdermal compositions for anticholinergic agents
US7198801B2 (en) 2000-08-03 2007-04-03 Antares Pharma Ipl Ag Formulations for transdermal or transmucosal application
ES2283425T3 (en) * 2000-08-03 2007-11-01 Antares Pharma Ipl Ag NEW COMPOSITION FOR THE TRANSDERMAL AND / OR TRANSMUCTIVE ADMINISTRATION OF ACTIVE COMPOUNDS THAT ENSURE ADEQUATE THERAPEUTIC LEVELS.
CA2437899C (en) 2001-02-13 2012-05-15 Gregory M. Glenn Vaccine for transcutaneous immunization against etec-caused traveler's diarrhea
ATE502657T1 (en) 2001-05-01 2011-04-15 Av Topchiev Inst Petrochemical TWO-PHASE WATER-ABSORBING BIOADHESIVE COMPOSITION
US6659985B2 (en) 2002-01-30 2003-12-09 Southern College Of Optometry Method to use transdermal administration of androgens to the adnexa of the eye
GB0210397D0 (en) 2002-05-07 2002-06-12 Ferring Bv Pharmaceutical formulations
AU2003240824B9 (en) * 2002-05-31 2008-09-25 University Of Mississippi Transmucosal delivery of cannabinoids
US20040105881A1 (en) * 2002-10-11 2004-06-03 Gregor Cevc Aggregates with increased deformability, comprising at least three amphipats, for improved transport through semi-permeable barriers and for the non-invasive drug application in vivo, especially through the skin
US7241456B2 (en) * 2002-10-25 2007-07-10 Australian Importers Ltd. Formulations for topical delivery of bioactive substances and methods for their use
MXPA06003316A (en) 2003-10-10 2006-06-08 Antares Pharma Ipl Ag Transdermal pharmaceutical formulation for minimizing skin residues.
US20050191338A1 (en) * 2004-01-30 2005-09-01 Lifeng Kang Transdermal drug delivery composition comprising a small molecule gel and process for the preparation thereof
JP5594925B2 (en) 2004-01-30 2014-09-24 コリウム インターナショナル， インコーポレイテッド Rapidly dissolving film for active substance delivery
US20050209319A1 (en) * 2004-03-18 2005-09-22 Xenoport, Inc. Treatment of local pain
WO2005110418A2 (en) 2004-05-07 2005-11-24 Phytotox Limited Transdermal administration of phycotoxins
US7666914B2 (en) * 2004-06-03 2010-02-23 Richlin David M Topical preparation and method for transdermal delivery and localization of therapeutic agents
EP1811961A2 (en) * 2004-11-12 2007-08-01 Idea Ag Extended surface aggregates in the treatment of skin conditions
WO2006090839A1 (en) * 2005-02-25 2006-08-31 Hisamitsu Pharmaceutical Co., Inc. Medicine for external application containing anti-inflammatory agent and soy lecithin
WO2007124250A2 (en) 2006-04-21 2007-11-01 Antares Pharma Ipl Ag Methods of treating hot flashes with formulations for transdermal or transmucosal application
WO2006125642A1 (en) 2005-05-27 2006-11-30 Antares Pharma Ipl Ag Methods and apparatus for transdermal or transmucosal application of testosterone
TWI366460B (en) 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
CA2988753A1 (en) 2007-08-06 2009-02-12 Serenity Pharmaceuticals, Llc Methods and devices for desmopressin drug delivery
US20110052738A1 (en) * 2008-01-17 2011-03-03 Gary Dean Bennett Topical pain formulation
WO2009110205A1 (en) 2008-03-04 2009-09-11 ナガセケムテックス株式会社 Agent for increasing the quantity of hyaluronic acid
RU2517594C2 (en) 2008-04-01 2014-05-27 Антиподиан Фармасьютикалз, Инк. Compositions and methods of skin care
US20090258070A1 (en) 2008-04-15 2009-10-15 John Burnier Topical LFA-1 antagonists for use in localized treatment of immune related disorders
PT3225250T (en) 2008-05-21 2019-10-15 Ferring Bv Orodispersible desmopressin for increasing initial period of sleep undisturbed by nocturia
US20100286045A1 (en) 2008-05-21 2010-11-11 Bjarke Mirner Klein Methods comprising desmopressin
US11963995B2 (en) 2008-05-21 2024-04-23 Ferring B.V. Methods comprising desmopressin
EP2376633A1 (en) 2008-12-17 2011-10-19 AVI BioPharma, Inc. Antisense compositions and methods for modulating contact hypersensitivity or contact dermatitis
WO2010091124A2 (en) 2009-02-03 2010-08-12 Microbion Corporation Bismuth-thiols as antiseptics for epithelial tissues, acute and chronic wounds, bacterial biofilms and other indications
US9782454B2 (en) 2010-04-22 2017-10-10 Longevity Biotech, Inc. Highly active polypeptides and methods of making and using the same
US20120083452A1 (en) * 2010-09-30 2012-04-05 Perricone Nicholas V Topical Anesthetic Uses of Szeto-Schiller Peptides
PL2704704T3 (en) 2011-05-03 2019-04-30 Dupont Nutrition Biosci Aps Probiotic bacteria for the topical treatment of skin disorders
CN103764150A (en) 2011-06-29 2014-04-30 阿勒根公司 Alcaftadine for use in treatment of urticaria
CN104884065B (en) 2012-09-21 2019-01-01 强烈治疗剂公司 The method for the treatment of cancer
US9789164B2 (en) 2013-03-15 2017-10-17 Longevity Biotech, Inc. Peptides comprising non-natural amino acids and methods of making and using the same
AU2014293140A1 (en) 2013-07-23 2016-03-03 Serenity Pharmaceuticals Llc Methods and compositions comprising desmopressin in combination with a 5-alpha reductase inhibitor
US9814753B2 (en) 2013-07-23 2017-11-14 Serenity Pharmaceuticals Llc Methods and compositions comprising desmopressin in combination with a beta-3-adrenergic receptor agonist
KR20220140042A (en) 2013-11-15 2022-10-17 온코슈틱스 인코포레이티드 7-benzyl-4-(2-methylbenzyl)-2,4,6,7,8,9-hexahydroimidazo[1,2-a]pyrido[3,4-e]pyrimidin-5(1h)-one, salts thereof and methods of use
US20150182451A1 (en) * 2013-12-27 2015-07-02 The Dial Corporation Cleansing composition for hormone deposition
WO2016025945A1 (en) 2014-08-15 2016-02-18 The Johns Hopkins University Technology Ventures Composite material for tissue restoration
ES2923438T3 (en) 2014-11-20 2022-09-27 Serenity Pharmaceuticals Llc Compositions comprising low doses of desmopressin in combination with an alpha-adrenergic receptor antagonist
PL3250208T3 (en) 2015-01-30 2021-04-06 Oncoceutics, Inc. 7-BENZYLO-4- (4- (TRIFLUOROMETHYL) BENZYLO) -1,2,6,7,8,9-HEXAHYDROIMIDAZO [1,2-A] PYRIDO [3,4-E] PYRIMIDIN-5 (4H) - HE AND HIS SALTS AND THEIR APPLICATION IN THERAPY
JPWO2016186157A1 (en) * 2015-05-19 2018-03-08 株式会社 メドレックス Transdermal solution
EP3337464B1 (en) 2015-08-17 2022-03-09 The Johns Hopkins University In situ forming composite material for tissue restoration
BR112018015590A2 (en) 2016-01-29 2019-10-01 Oncoceutics Inc g protein coupled receptor (gpcr) modulation by imipridones
EP3562943A1 (en) 2016-12-30 2019-11-06 Nogra Pharma Limited Compositions of smad7 antisense oligonucleotide and methods of treating or preventing psoriasis
CA3099733A1 (en) 2018-05-09 2019-11-14 The Johns Hopkins University Nanofiber-hydrogel composites for enhanced soft tissue replacement and regeneration
US12161781B2 (en) 2018-05-09 2024-12-10 The Johns Hopkins University Nanofiber-hydrogel composites for cell and tissue delivery
ES2986149T3 (en) 2018-10-09 2024-11-08 Univ Rochester Treatment of vulvovaginal disorders
WO2020152350A1 (en) 2019-01-25 2020-07-30 Nogra Pharma Limited Compositions for use in preventing acne
EP4240347A1 (en) * 2020-11-06 2023-09-13 Zelira Therapeutics Operations Pty Ltd Cannabinoid encapsulation technology
WO2024156864A2 (en) 2023-01-27 2024-08-02 Nogra Pharma Limited Fatty acid compounds and methods of use
WO2024173675A1 (en) 2023-02-16 2024-08-22 University Of Rochester Improving glymphatic-lymphatic efflux
WO2024226871A1 (en) 2023-04-27 2024-10-31 Mccord Darlene E Compositions and methods of dissolving biofilm to promote wound healing
WO2025038701A1 (en) 2023-08-15 2025-02-20 Tryglobal Ip, Holdings Llc Composite materials and methods of using the same for wound healing and antimicrobial applications

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2001334B (en) * 1977-07-19 1982-03-03 Fisons Ltd Pressurised aerosol formulation
FR2478485A1 (en) * 1980-03-24 1981-09-25 Oreal COSMETIC OR PHARMACEUTICAL COMPOSITIONS IN THE FORM OF STABLE EMULSIONS OF THE OIL-IN-WATER TYPE
US4699776A (en) * 1985-06-28 1987-10-13 R. P. Scherer Corporation Suppositories containing analgesics, antipyretics or anti-inflammatory agents
JPS62123132A (en) * 1985-11-21 1987-06-04 Michio Nakanishi Composition for remedying bronchial asthma

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7867480B1 (en) 1999-01-27 2011-01-11 Gregor Cevc Non-invasive vaccination through the skin
US7927622B1 (en) 1999-01-27 2011-04-19 Gregor Cevc Methods of transnasal transport/immunization with highly adaptable carriers
US7459171B2 (en) 1999-07-05 2008-12-02 Idea Ag Method for the improvement of transport across adaptable semi-permeable barriers

Also Published As

Publication number Publication date
DE3887156T2 (en) 1994-04-28
JP2714413B2 (en) 1998-02-16
DE3887156D1 (en) 1994-02-24
DE3887156T3 (en) 1998-04-16
US4783450A (en) 1988-11-08
WO1988007871A1 (en) 1988-10-20
JPH02502994A (en) 1990-09-20
EP0382716B2 (en) 1998-01-28
EP0382716A1 (en) 1990-08-22

Similar Documents

Publication Publication Date Title
EP0382716B1 (en) Use of commercial lecithin as skin penetration enhancer
EP2373346B1 (en) Ibuprofen for topical administration
JP2011074086A (en) Transmucosal drug delivery system
EP0261429A1 (en) Penetration enhancement systems and the preparation thereof
RU99114830A (en) THERAPEUTIC MEANS
JPH08502288A (en) Pharmaceutical composition and method for treating sensational symptoms
JP2939264B2 (en) Penetration augumenting composition
JPH02503672A (en) Fatty acids and their short chain esters as penetration enhancers in aqueous systems
US3428728A (en) Timed release sublingual medications
AU685741B2 (en) Sprayable analgesic composition and method of use
JP5161472B2 (en) Analgesic composition
JPS61280435A (en) Lymph orienting preparation of cyclosporin
US5401728A (en) Lecithin based topical liniment
JP2905210B2 (en) Transdermal and transmucosal absorption enhancers and transdermal and transmucosal preparations
JPS6092214A (en) Composition for filling soft capsules
EP0238198A3 (en) Method of modifying the lipid structure function and expression of cell membranes and pharmaceutical compositions for use therein
JP3277735B2 (en) Composition for promoting absorption of naphthoic acid derivative
JP4710240B2 (en) Pharmaceutical composition
JP2005289906A (en) Pharmaceutical composition
JPS61134315A (en) antipyretic analgesic
JPH0113449B2 (en)
JPH11302189A (en) Common cold composition
EP0239527A2 (en) Composition adopted for use as a transdermal formulation
JPS60218318A (en) Composition for filling soft capsules
US20040241217A1 (en) Method for administration of immune modulators in systemic and localized immune disorders

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19891013

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

17Q First examination report despatched

Effective date: 19921201

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

REF Corresponds to:

Ref document number: 99960

Country of ref document: AT

Date of ref document: 19940115

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3887156

Country of ref document: DE

Date of ref document: 19940224

ET Fr: translation filed
ITF It: translation for a ep patent filed
EPTA Lu: last paid annual fee
PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

26 Opposition filed

Opponent name: HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

Effective date: 19941004

NLR1 Nl: opposition has been filed with the epo

Opponent name: HENKEL KOMMANDITTGESELLSCHAFT AUG AKTIEN

EAL Se: european patent in force in sweden

Ref document number: 88903109.2

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PUAH Patent maintained in amended form

Free format text: ORIGINAL CODE: 0009272

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: PATENT MAINTAINED AS AMENDED

27A Patent maintained in amended form

Effective date: 19980128

AK Designated contracting states

Kind code of ref document: B2

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

REG Reference to a national code

Ref country code: CH

Ref legal event code: AEN

Free format text: AUFRECHTERHALTUNG DES PATENTES IN GEAENDERTER FORM

NLR2 Nl: decision of opposition
ITF It: translation for a ep patent filed
ET3 Fr: translation filed ** decision concerning opposition
NLR3 Nl: receipt of modified translations in the netherlands language after an opposition procedure
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19991213

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19991229

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 20000203

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20000204

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20000210

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 20000302

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20000303

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20000407

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20000413

Year of fee payment: 13

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010318

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010318

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010318

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010319

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010331

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010331

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010331

BERE Be: lapsed

Owner name: WARNER-LAMBERT CY

Effective date: 20010331

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20011001

EUG Se: european patent has lapsed

Ref document number: 88903109.2

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20010318

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20011130

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 20011001

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020101

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050318